Trimethylamine → HCID 21480500, compound

Participants

Reaction Steps

To a solution of the product from Step D (1.37 g, 5.25 mmol and trimethylamine (2.12 g, 21.0 mmol) in methylene chloride (100 mL) at 0° C. was added p-toluenesulfonyl chloride (2.50 g, 13.13 mmol). The mixture was stirred for 3 h, cooled (about 7° C.) overnight, and 2-methoxyethylamine (5 mL) was added, followed by stirring for 2 h at ambient temperature and heating at reflux temperature for 2 h. A saturated solution of sodium bicarbonate (80 mL) was added to the reaction mixture which was extracted with ethyl acetate (2×80 mL). The combined extracts were evaporated to a residue which was purified by column chromatography (silica, ethyl acetate) to give a viscous oil (0.98 g, 62%). Dissolution of the oil in ethyl acetate (50 mL) and treatment with 2N HCl/EtOH (2 mL) provided a crystalline solid which was collected by filtration and dried to give a colorless solid: mp 208°-210° C.

Provenance & Evidence